Key West Events

Key West Events

There are so many Key West events, so much to do in Key West all year, we can’t even list them all! But here’s a pretty good listing of the major events, month by month. Scroll down to any month and find out which Key West eventsare happening when you are in town.



Annual Key West Literary Seminar

Famous authors come to Key West for four days of workshops, panel discussions, and receptions. Each year there’s a different theme. All writers and non-writers welcome!

Key West House and Garden Tour, Part Two

See exquisitely-designed gardens, architecture and interiors of some of Key West’s finest homes. Like taking a stroll through an architecture magazine or a home decorator’s brochure. Just beautiful.

Florida Keys Seafood Festival

Corner of Truman and Eisenhower is a wonderful community park. The seafood festival has live music, and is billed as a family event. Face painting, activities and of course seafood galore. Put on by the Florida Keys Commercial Fishermen’s Association and the University of Florida’s Monroe County Extenstion Services Office. Admission is free.

Sculpture Key West

This annual public art festival starts in January and runs through the end of February. Large sculpture appears in places like Fort Zachary Taylor State Park and parks throughout Key West.

Key West Race Week

Top notch sailors come to town every year and compete in yacht races held throughout the week in mid-January.

King Mackerel Tournamant

This is usually the last weekend in January, sponsored by local bar and restaurant. Cash prizes for the the kingfish, lots of fun.


January is a big month for theater-going individuals. Check local listings for what’s playing and where.

Key West Symphony

January is their season for concerts by the Key West Symphony.

Key West Craft Show

Every year artists and crafts people show their work in Old Town on Whitehead Street. Make a day of it and head out to Whitehead Pier, at the end of the street on the Ocean side.


Old Island Days Art Festival

Also on Whitehead Street, like the Craft Show in January. Only this time it’s fine art from galleries.

Kelly McGillis Classic International Girls’ and Women’s Flag Football Championship

Part of an international tournament cycle for women’s flag football, the Kelly McGillis Classic is a four day competition in Key West. Promotes leadership skills for girls and a stronger female in society, according to the league’s website. Kelly McGinnis plays in the games and also acts in local productiond while here in February.

Key West Antiques Show

This is a benefit for the Key West Art & Historical Society. Dealers come from all over for the show and sale.

Civil War Heritage Festival

This is held at our very own spot of civil war history, Fort Zachary. Re-enactments and special tours of the fort, which is now a Florida State Park.

Key West House & Garden Tour, Part Three

The tours continue in the third installment, in February.


Key West Boat Show

The show features a wide selection of new boats from many of the largest boat dealers in the Florida Keys. The large nautical flea market offers boaters and fishing enthusiasts everything from new and used rods and reels, to top-of-the-line Sperry boat shoes, hard-to-find boat accessories and nautical art.

Key West Pops

Look for concerts in March from the Key West Pops Orchestra.

Conch Shell Blowing Contest

Funny contests aimed at kids but anyone can enter. Just make some music with your shell and you might be a winner.

Sculpture Key West

Sculpture exhibits all over town continue throughout March.

Island Opera Theater

Island Opera Theater has shows in March. Held at Tennessee Williams Theatre at Florida Keys Community College.

Key West Fishing Tournament

This tournament starts with a kick-off party in Key West, and continues through November. Open to the public, anyone can enter.

Key West Home & Garden Tour, Final Part

This is the fourth and final segment of the house and garden tour series that runs through winter and early spring.


At Key West Botanical Garden, 5210 College Road, vendors sell all types of exotic plants. The Key West Botanical Garden in on Stokc Island, just over the bridge from the island of Key West.


Keys Choral Concert Under The Stars

Local singing group give a concert outdoors under the stars. New location each year.

Key West Events

Hemingway Days


More Info on Key West Events

Sculpture Key West

Sculpture Key West’s final month.

Robert Frost Poetry Festival

Poetry and haiku workshops, readings, and contests at the Robert Frost Cottage and the Heritage House Museum.

World Sailfish Championship

Three days of fishing and three nights of gala fun.

Taste of Key West

Head downt to the waterfront in Old Town for event where Key West restaurants provide samples of their fine food. Benefit AIDS Help Inc.

Red Barn Theater

This local theater has shows in April so watch for their schedule.

Conch Republic Independence Celebration

Whacky tribute to Key West’s bid at independece from the United States in the early 1980s. Races, drag race, parties and fun.


Shell Key West Challenge

Offhore fishing tournament to benefit Diabetes Research Institute.

Yamaha Dolphin Masters Invitational

This dolphin tournament has a legendary first prize.

Key West Songwriters’ Festival

Songwriters perform in lots of downtown Duval Street bars and restaurants, great for the live music scene.

Waterfront Playhouse

This local theater gives shows in season, so check out their schedule for showtimes.


PrideFest Key West

Celebrating diversity and gay and lesbian culture. Parade, events, and good times.

Goombay Summer Fest

Bahama Village comes alive with live music, food vendors, and lots of family events. Celebrates Caribbean culture.

IGFA Junior Angler World Championship Tournament

Kid compete to catch dozens of species. Catch and release tournament.

Conch Republic Ladies Dolphin Tournament

Ladies only! Big cash prizes as women compete for Dolphin.

Key West Gator Club Dolphin Derby

Raise money for scholarships by fishing for Dolphin…what could be better?

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